- THEOPHYLLINE DERIVATIVES WITH NEMATOCIDAL ACTIVITY, THEIR AGRONOMIC COMPOSITIONS AND RELATIVE USE
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The present invention relates to theophylline derivatives having general formula (I) agronomic compositions containing said compounds having formula (I) and analogous compounds having formula (XVI) and their use for the control of nematodes in agricultural crops. These compounds advantageously prove to be both effective against parasites and free of phytotoxicity.
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Page/Page column 49
(2020/08/22)
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- Design, synthesis and biological evaluation of theophylline containing variant acetylene derivatives as α-amylase inhibitors
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A novel pharmacophore with theophylline and acetylene moieties was constructed by using a fragment-based drug design and a series of twenty theophylline containing acetylene conjugates were designed and synthesized, and all the compounds were evaluated by enzyme-based in vitro α-amylase inhibition activity. The in vitro evaluation revealed that most of the compounds displayed good inhibitory activities, and among them nine analogs 13–15, 20, 21 and 24–27 were exhibited more or nearly as equipotent inhibitory activity with IC50 values 1.11 ± 0.07, 1.14 ± 0.17, 1.07 ± 0.01 and 1.21 ± 0.03, 1.33 ± 0.09, 1.17 ± 0.01, 1.05 ± 0.02, 1.61 ± 0.04, 1.02 ± 0.03 μM respectively, as compared with standard, acarbose 1.37 ± 0.26 μM. Further, molecular docking simulation studies were done to identify the interactions and binding mode of synthesized analogs at binding site of α-amylase enzyme (PBD ID: 4GQR). Among the synthesized analogs, two compounds 25 and 27 were selected on the basis of α-amylase inhibition activity and evaluated for in vivo anti-diabetic activity by High Fat Diet-Streptozotocin (HFD-STZ) model in normal rats. At the dose of 10 mg/kg, bw, po these compounds have significantly reduced Plasma Glucose level in rats as compared to pioglitazone. The anti-diabetic activity results showed that the animal treated with the compounds 25 and 27 could better reverse and control the progression of the disease compared to the standard.
- Ruddarraju, Radhakrishnam Raju,Kiran, Gangarapu,Murugulla, Adharvana Chari,Maroju, Ravichandar,Prasad, Devarakonda Krishna,Kumar, Boyina Hemanth,Bakshi, Vasudha,Reddy, Nukala Shravya
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- Design, synthesis, anticancer activity and docking studies of theophylline containing 1,2,3-triazoles with variant amide derivatives
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A new series of theophylline analogues containing 1,2,3-triazoles with different amide groups (22-41) has been designed and synthesized, and their biological activities have been evaluated as potential anticancer agents. The anticancer activities of the synthesized compounds were studied in four cancer cell lines viz. lung (A549), colon (HT-29), breast (MCF-7) and melanoma (A375). Furthermore, these compounds were screened for computational ADME and Lipinski's analysis followed by molecular docking and binding energy calculations against the various therapeutic targets involved in cell proliferation. The in vitro results demonstrate that compounds 22, 27, 36 and 40 have pivotal anticancer activity. Among these, compounds 22 and 27 have significant cytotoxic activity in all three cell lines; the in silico docking studies also reveal that compounds 22, 27 and 36 have good dock scores, binding affinities and binding energies towards human epidermal growth factor receptor 2. This is the first report to demonstrate theophylline hybrids containing 1,2,3-triazoles as potential anticancer agents.
- Ruddarraju, Radhakrishnam Raju,Murugulla, Adharvana Chari,Kotla, Ravindar,Tirumalasetty, Muni Chandra Babu,Wudayagiri, Rajendra,Donthabakthuni, Shobha,Maroju, Ravichandar
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p. 176 - 183
(2017/02/05)
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- Theophylline process for the preparation of acetic acid
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The invention belongs to the field of chemical synthesis. In the prior art, the raw materials for synthesis of theophylline-7-acetic acid all contain chloroacetic acid, which has a strong toxicity, purchase channels of chloroacetic acid are strictly restricted, so the production of theophylline-7-acetic acid is largely affected. The invention provides a preparation method of theophylline-7-acetic acid, the preparation method comprises following steps: subjecting dimethyl FAU to react with sodium hydroxide water solution to form theophylline sodium salt, adding sodium chloroacetate water solution drop by drop, after the reaction solution is clear, maintaining the reactant pH in the range of 8 to 12 by adding Na2CO3 water solution. The yield of the product prepared by the preparation method provided by the invention has been improved to 90% or more, the content of the product reaches 99.9%, the quality of the product is stable and meets the requirement of pharmacopeia.
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Paragraph 0036-0040
(2017/01/09)
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- Design, synthesis, anticancer, antimicrobial activities and molecular docking studies of theophylline containing acetylenes and theophylline containing 1,2,3-triazoles with variant nucleoside derivatives
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A new series of theophylline containing acetylene derivatives (6a–6b and 7–13) and theophylline containing 1,2,3-triazoles with variant nucleoside derivatives (20–32) have been designed and synthesized. These compounds were screened for anticancer and antimicrobial activity. Further the computational docking and 2D QSAR were performed using MOE software to identify novel scaffolds. The results showed that compound 29 and 30 exhibit significant cytotoxic effect on all four cancer cells such as lung (A549), colon (HT-29), breast (MCF-7) and melanoma (A375) with IC50values of 2.56, 2.19, 1.89, 4.89?μM and 3.57, 2.90, 2.10, 5.81?μM respectively. Whereas quite different results were observed for these compounds in antimicrobial studies. Compounds 11, 21 and 26 have exhibited significant minimum inhibitory concentrations (MIC) against Staphylococcus aureus, Bacillus cereus, Escherichia coli and Pseudomonas aeruginosa. The docking studies demonstrate that compound 27, 28, 29 and 30 have good dock score and binding affinities with various therapeutic targets in cancer cell proliferation. In addition these compounds have shown acceptable correlation with bioassay results in the regression plots generated in 2D QSAR models. This is the first report to demonstrate the theophylline containing acetylene derivatives and theophylline containing 1,2,3-triazole nucleoside hybrids as potential anticancer and antimicrobial agents with comprehensive in silico analysis.
- Ruddarraju, Radhakrishnam Raju,Murugulla, Adharvana Chari,Kotla, Ravindar,Chandra Babu Tirumalasetty, Muni,Wudayagiri, Rajendra,Donthabakthuni, Shobha,Maroju, Ravichandar,Baburao,Parasa, Lakshmana Swamy
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p. 379 - 396
(2016/08/04)
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- N-(4-Arylpiperazinoalkyl)acetamide derivatives of 1,3- and 3,7-dimethyl-1H-purine-2,6(3H,7H)-diones and their 5-HT6, 5-HT7, and D2 receptors affinity
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A series of N-(arylpiperazinyl)acetamide derivatives of 1,3- and 3,7-dimethyl-1H-purine-2,6(3H,7H)-dione was synthesized and biologically evaluated in in vitro competition binding experiments for serotonin 5-HT6, 5-HT7, and dopamine D2 receptors. The structure-affinity relationships for this group of compounds allowed for determination of structural features responsible for receptor affinity. Among the investigated derivatives, compounds 5 and 12 with (2,3-dichlorophenyl)piperazine moiety were classified as potent dual 5-HT6/D2 receptors ligands, whereas compound 4, with 4-(benzo[d]isothiazol-3-yl)piperazine moiety, and compounds 8 and 15, with (2,3-dichlorophenyl)piperazine moiety, were classified as potent D2 receptor ligands.
- Zmudzki, Pawel,Satala, Grzegorz,Chlo-Rzepa, Grazyna,Bojarski, Andrzej J.,Popik, Piotr,Zajdel, Pawel
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- Potentiation of cADPR-induced Ca2+-release by methylxanthine analogues
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Caffeine and other methylxanthines are known to induce Ca2+-release from intracellular stores via the ryanodine receptor. In the present work, a range of caffeine analogues, in which methyl groups at the 1 and 7 positions were replaced with alkyl chains containing different functional groups (oxo, hydroxyl, propargyl, ester, and acids), were synthesized. These compounds were then screened for their ability to potentiate Ca2+-release induced by cADPR (an endogenous modulator of ryanodine receptors) in sea urchin egg homogenates. Two of the synthesized methylxanthines, 1,3-dimethyl-7-(7- hydroxyoctyl)xanthine (37) and 3-methyl-7-(7-oxooctyl)-1-propargylxanthine (66), were shown to be more potent than caffeine in potentiating cADPR- induced Ca2+-release, while 1,3-dimethyl-7-(5-ethylcarboxypentyl)xanthine (14) was shown to be more efficacious. The development of new methylxanthine analogues may lead to a better understanding of ryanodine receptor function and could possibly provide novel therapeutic agents.
- Cavallaro, Rosaria A.,Filocamo, Luigi,Galuppi, Annamaria,Galione, Antony,Brufani, Mario,Genazzani, Armando A.
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p. 2527 - 2534
(2007/10/03)
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- Studies of reactions within molecular complexes: Alkaline hydrolysis of substituted phenyl benzoates in the presence of xanthines
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Complexation with caffeine and theophylline-7-acetate depresses the rate of alkaline hydrolysis of substituted phenyl benzoates and is consistent with the formation of molecular complexes with 1:1 stoichiometry between the hosts and esters; stacking of the xanthines is excluded as an explanation in the range of concentrations studied. Bronsted-type correlations have been determined for the rate and complexation constants and for the transition-state binding constants. Development of effective charge in the transition state of the reactions in bulk solvent is slightly less than that in the host-ester complex, consistent with a similar electronic environment in both states. The negative Bronsted β values for Ks indicate that the interactions between ester and hosts involve electron donation to the host from the ester. Inhibition of hydrolysis is attributed to repulsion of the hydroxide ion from the host-ester complex by the extra hydrophobicity engendered by the xanthine host, as well as by the weaker binding of the transition state to the host compared with that in the host-ester complex.
- Pirinccioglu, Necmettin,Williams, Andrew
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- Process for obtaining complex of 3-methoxy-N-methylmorphinan with 7-theophyllineacetic acid (1:2)
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A complex of 3-methoxy-N-methylmorphinan with 7-theophyllineacetic acid (1:2) is prepared by reacting the reactive materials in a polar solvent. The complex has antitussive activity.
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